Eicosanoid derivatives
a technology of eicosanoid derivatives and derivatives, which is applied in the field of eicosanoid derivatives, can solve the problems of not being widely used as therapeutics, and achieve the effect of suppressing the response of nrcms and increasing extracellular ca2+- concentrations
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example 2
Synthesis of (5Z,11Z)-16-(3-Ethyloxirane-2-yl)hexadeca-5,11-dienoic acid (2)
[0142]
[0143]Oct-1,7-diyne (9.0 g, 84.9 mmol; G F Smith) was alkylated with 2-(4-bromobutoxy)-tetrahydropyran (15 g, 63.68 mmol) as described above for the synthesis of 2-(pentadeca-5,14-diynyloxy)tetrahydropyran to give 2-(dodeca-5,11-diynyloxy)tetrahydropyran (10.85 g, 65%) as a colorless oil. TLC: 10% EtOAc / hexanes, Rf≈0.6; 1H NMR (400 MHz, CDCl3) δ 4.57 (t, J=2.5 Hz, 1H), 3.82-3.87 (m, 1H), 3.70-3.77 (m, 1H), 3.46-3.51 (m, 1H), 3.36-3.42 (m, 1H), 2.14-2.20 (m, 6H), 1.93 (t, 1H, J=2.5 Hz), 1.46-1.72 (m, 14 H).
[0144]
[0145]A solution of carbon tetrabromide (10.8 g, 32.94 mmol) in CH2Cl2 (25 mL) was stirred into a 0° C. solution of triphenylphosphine (8.6 g, 32.94 mmol) and oct-5(Z)-en-1-ol (2.8 g, 14.06 mmol) in dry CH2Cl2 (100 mL) under an argon atmosphere. After 30 min, the reaction mixture was washed with water (75 mL), brine (50 mL), dried over anhydrous Na2SO4, and all volatiles were removed under reduc...
example 3
Synthesis of (8Z,14Z)-16-(3-Ethyloxirane-2-yl)hexadeca-8,14-dienoic Acid (3)
[0159]
[0160]Heptane-1,7-diol (36.0 g, 272 mmol; Alfa Aesar) and aq. 48% HBr (38 mL) were heated under reflux in benzene (400 mL) with water removal using a Dean-Stark apparatus. After 12 h, all volatiles were removed in vacuo and the residue was purified by SiO2 column chromatography using a gradient of 10-30% EtOAc / hexanes as eluent to give 7-bromoheptan-1-ol (26.22 g, 62%) as colorless oil. TLC: 50% EtOAc / hexanes, Rf≈0.4; 1H NMR (400 MHz, CDCl3) δ 3.61 (t, 2H, J=7.1 Hz), 3.39 (t, 2H, J=6.8 Hz), 1.80-1.88 (m, 2H), 1.52-1.58 (m, 2H), 1.30-1.46 (m, 6H).
[0161]
[0162]7-Bromoheptane-1-ol (11.0 g, 56.7 mmol) from above was protected as its THP ether as described previously to give 2-(7-bromoheptyloxy)tetrahydro-2H-pyran (14.50 g, 92%) as colorless oil. TLC: 10% EtOAc / hexanes, Rf≈0.5; 1H NMR (400 MHz, CDCl3) δ 4.58 (m, J=2.5 Hz, 1H), 3.84-3.88 (m, 1H), 3.68-3.77 (m, 1H), 3.46-3.3.51 (m, 1H), 3.33-3.43 (m, 3H), 1.80...
example 4
Synthesis of 16-[(Z)-3-Ethyloxiranyl]hexadec-11(Z)-enoic Acid (4), 16-[(Z)-3-Ethyloxiranyl]hexadec-5(Z)-enoic Acid (7), and 16-[(Z)-3-Ethyloxiranyl]hexadecanoic Acid (8)
[0175]
[0176]A stream of dry air was passed through a stirring solution of hydrazine hydrate (400 mg, 12 mmol, 20 equiv), methyl 16-[(Z)-3-ethyloxiranyl]hexadeca-5(Z),11(Z)-dienoate (200 mg, 0.60 mmol), and CuSO4.5H2O (10 mg) in ethanol (5 mL). The stream of air was passed through EtOH to saturated it with ethanol and help maintain the reaction volume. After 12 h, the reaction mixture was passed through a short pad of silica gel and the filter cake was washed with dichloromethane (3×10 mL). The combined filtrates were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was resolved into its components by AgNO3-impregnated PTLC using 2% CH2Cl2 / benzene: Rf≈0.2, 0.4, 0.55, and 0.85 for methyl 16-[(Z)-3-ethyloxiranyl]hexadeca-5(Z),11(Z)-dienoate, methyl 16-[(Z)-3-ethyloxiranyl]hexadec-11(Z)-enoate, methyl ...
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